Alan Bersin may be thumbing yet another ride on Barack Obama’s political appointment highway.

Though the Obama administration’s second-term housecleaning begins soon, one controversial San Diegan is given good odds to hang around another four years in one capacity or another. Alan Bersin, currently assistant secretary of international affairs at Homeland Security, is a longtime friend of Bill and Hillary Clinton, having gone to Yale Law and Oxford University on a Rhodes scholarship.

Brooklyn born, Bersin moved to Los Angeles and met Lisa Foster, wealthy heiress to San Diego’s garment-making and border-area-real-estate Ratner fortune. After marrying, the couple moved to San Diego, and Bersin became local chairman of Bill Clinton’s 1992 presidential campaign. Following the election, Clinton named him U.S. attorney here.

Though Bersin had a rocky tenure, criticized by some for forcing illegal border crossers east into the perilous backcountry, he also became Southwest “border czar,” named by Clinton’s attorney general Janet Reno. In 1997, he endorsed a San Ysidro real estate development at the same time he and family members owned property near the frontier with Mexico.

But the fireworks really began for Bersin in 1998, when instead of heading to Washington to assume a high-ranking Justice Department post as widely expected, he became superintendent of the San Diego Unified School District. Seven years and many privatization battles with the teachers’ union later, Bersin was unceremoniously let go by a newly elected school board majority. The Democrat became GOP governor Arnold Schwarzenegger’s secretary of education, and later Republican San Diego mayor Jerry Sanders appointed him to the board that runs San Diego’s international airport.

Then came the 2008 election of Barack Obama, and Bersin wound up as assistant secretary for international affairs and special representative for border affairs at the Department of Homeland Security. The president named him commissioner of customs and border protection but was forced to use a so-called recess appointment after a Senate committee failed to act on the nomination and details emerged of reporting problems regarding his household staff in Point Loma. When that gig timed out last December, Bersin was made assistant secretary of international affairs and chief diplomatic officer of Homeland Security.

Bersin and his extended family have long been heavy donors to Democratic causes, including Obama’s presidential campaign. Before he got his job in the new administration, Bersin gave $28,500 to the Democratic White House Victory Fund in July 2008; $2300 to the Obama Victory Fund the same month; and $6500 to the Committee for Change that October. He also kicked in $28,500 to the Democratic National Committee Services Corporation.

This year, records show, Bersin hasn’t made any contributions, though daughter Alissa by his first marriage gave $500 on August 25. She works for the McDevitt Company, a high-end retail real estate firm from Philadelphia. According to a May 2010 wedding notice in the New York Times, Alissa “helps design and execute expansion strategies for retailers” and has a bachelor’s degree from Harvard and a master’s in European cinema studies from England’s University of Bath. Her husband Zachary Miller coproduced 2009’s The Messenger, a war drama starring Woody Harrelson and Ben Foster and directed by Israeli screenwriter and former journalist Oren Moverman. Miller gave Obama $288 in 2008.

Bersin’s mother-in-law, Pauline Foster of Rancho Santa Fe, gave $2500 to the winning congressional campaign of Democrat Scott Peters, as well as $1750 to ex–Democratic assemblywoman Lori Saldaña, who narrowly lost to Peters in the primary. Foster also gave $2000 to Democratic congresswoman Susan Davis.

Her daughter, Karen Silberman, gave $3500 to Peters. Karen’s husband, Jeff Silberman, son of ex–federal prison inmate Richard Silberman, who was once married to ex–San Diego mayor Susan Golding, gave $5000 to Peters. In addition, Jeffrey gave a total of $500 to Obama and $2500 to the U.S. Senate campaign of Wisconsin Democrat Tammy Baldwin, who beat former GOP governor Tommy Thompson, thus becoming the first openly gay senator in history.